Rolling Stone magazine covers at the Rolling Stone 50 Years exhibit at the Rock and Roll Hall of Fame, Cleveland.
Photograph: Tony Dejak/AP

It is the magazine that described investment bank Goldman Sachs as “a great vampire squid wrapped around the face of humanity”, George W Bush as the “worst president in history” and featured a photo of a naked John Lennon curled around Yoko Ono on its front page.

But after almost 50 years of seminal covers and epoch-shifting articles, the owners of Rolling Stone have put the title up for sale amid financial difficulties.

Founded by Jann Wenner in 1967 when he was a 21-year-old hippy student in California, Wenner now runs the rock’n’roll magazine turned liberal cheerleader with his son Gus, president of the family publishing company.

On Sunday, the pair announced they were planning to sell their remaining stake in the title that has ruthlessly skewered public figures and helped to launch the careers of such influential creatives as photographer Annie Leibovitz and the gonzo journalist Hunter S Thompson.

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“There’s a level of ambition that we can’t achieve alone,” Gus Wenner, 27, told the New York Times in an interview to announce the search for a buyer. “So we are being proactive and want to get ahead of the curve.”

The pressure on the publishing industry from the rise of the internet, a costly libel battle, and financial deals that with the benefit of hindsight look like unwise have combined to prompt the Wenners to consider their options.

Jann Wenner says he wants to find a buyer that understands Rolling Stone and has “lots of money”. The 71-year-old said: “Rolling Stone has played such a role in the history of our times, socially and politically and culturally. We want to retain that position.” Both Wenners are keen to remain involved with the magazine after it is sold.

Jann Wenner founded Rolling Stone as a student at Berkeley alongside Ralph J Gleason, a columnist and jazz critic at the San Francisco Chronicle who shared his passion for music. Lennon appeared on the cover of the first issue.

The magazine still revolves around music, film and TV, but has also become renowned for in-depth features and interviews on US culture that have become news themselves.

These include Matt Taibbi’s evisceration of US investment bank Goldman Sachs in 2009 as the world reeled from the worst financial crisis since 1929. Taibbi famously described how Goldman alumni ended up in powerful government positions around the world, writing of the bank: “The world’s most powerful investment bank is a great vampire squid wrapped around the face of humanity, relentlessly jamming its blood funnel into anything that smells like money.”

Rolling Stone’s liberal ideology has also evolved into one of its hallmarks. It has published high-profile interviews with Bill Clinton and Barack Obama, both conducted by Jann Wenner himself, and in August it put a photo of Canadian prime minister Justin Trudeau on its cover with the headline: “Why can’t he be our president?”

It has been a constant critic of US president Donald Trump and pilloried George W Bush with satirical cartoons on its front page, including one headlined: “The worst president in history?”

The cover of Rolling Stone frequently carries provocative images and starring on its cover remains a sought-after honour for musicians and actors. Leibovitz was behind many of Rolling Stone’s most memorable early covers, including the photo of Lennon and Ono in 1981. Lennon was shot dead just hours after the photograph was taken.

Other celebrated contributors to the magazine include Thompson and Tom Wolfe. Thompson’s novel Fear and Loathing in Las Vegas was serialised by Rolling Stone and eventually was adapted into a film, with Johnny Depp playing Thompson.

Jann Wenner with singer-songwriter and actor Bette Midler at the premiere of the Rolling Stone Covers Tour in 1998. Photograph: Kathy Willens/AP

However, the magazine’s reputation – and finances – were badly damaged when it retracted a 2014 story about an alleged gang-rape at the University of Virginia, with a review finding that Rolling Stone did not undertake basic journalistic procedures to verify the facts. The magazine was last year ordered to pay $3m (£2.2m) in damages over the article after a high-profile trial.

Wenner’s decision to buy back a 50% stake in magazine US Weekly for $300m in 2006 could also be considered an error. He had sold the stake to Walt Disney for just $40m five years earlier and buying it back left the family publisher saddled with debt.

His son attempted to deal with the financial pressures on the company earlier this year by selling US Weekly and Men’s Journal, another of Rolling Stone’s sister titles, to American Media. BandLab Technologies, a Singapore-based music company, also bought a 49% stake in Rolling Stone last year.

Both American Media – publisher of supermarket tabloids including the National Enquirer – and BandLab are seen as contenders to take control of Rolling Stone. If American Media buys the title, it would mark a sharp change in owners’ ideologies. The tabloid empire is led by David Pecker, an ardent Trump ally.

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Looking back on the past 50 years, Jann Wenner said he never expected Rolling Stones to branch into politics.

“Back then, if it was a viable music magazine, that would have been the biggest ambition,” Wenner said. “I didn’t envision that it would be a magazine that would be involved in presidential elections and we’d be going to the White House and interviewing the president on Air Force One.

“I think Rolling Stone had a purpose, a mission and a sensibility that came from the beginnings of the postwar baby boom. There was a point of view that was being informed by the Beatles, the Stones and Dylan and there was a lot of commitment to making the world a better place, as it were.”

Cover to cover: a potted history of Rolling Stone

1967: Jann Wenner creates Rolling Stone magazine with Ralph J Gleason, a music critic. The cover of the first issue features John Lennon.

1981: The 22 January edition of Rolling Stones features arguably its most famous cover – a naked John Lennon wrapped around Yoko Ono in the foetal position. The photo was taken by Annie Leibovitz hours before Lennon was shot and the magazine, which was dedicated to the Beatles star, featured the last ever interview with him.

2001: Jann Wenner sells a 50% stake in Rolling Stone’s sister title Us Weekly for $40m to Walt Disney. Five years later he buys it back for $300m.

2006: Rolling Stone, which has become increasingly political, targets George W Bush with satirical cartoons on its cover.

2009: Matt Taibbi’s seminal article on Goldman Sachs is published, which describes the investment bank as “a great vampire squid wrapped around the face of humanity”.

2010: Barack Obama fires Gen Stanley McChrystal, the head of American forces in Afghanistan, after a Rolling Stone article headlined “The Runaway General” in which he and his aides are quoted as critical of the president and his approach.

2013: Jann Wenner appoints his son, Gus, as head of Rollingstone.com, a sign that the younger Wenner is becoming influential in the family media business.

2014: A Rolling Stone article makes allegations about a gang rape at the University of Virginia. After commentators question the article and the Washington Post highlights factual inaccuracies, the magazine commissions an investigation by Columbia Graduate School of Journalism, which is damning of the feature. Rolling Stone eventually pays out $3m in damages.